I didn't realize the -D option was only in OpenSSH until Bitt mentioned it. So, I guess that's out, unless you want to switch over to OpenSSH, which might not be a bad idea.
Tried that (see above). OpenSSH doesn't work with windows unless you you cygwin and that's getting pretty nasty.
I'm still not sure I'm seeing how this works though. Can you explain how you have GAIM set up to use the tunnel? I don't see what options you'd put in. You must have done the -D trick, with SOCKS and localhost, or something. But how do things know to get to login.oscar.aol.com:5190? Do you specify that somewhere? Not seeing that.
Also, there are small proxies out there, like ReAIM, that are made specifically to be an AIM proxy. I've never tried any of them, but I'm sure one would work for you.
This might work, and that may be what I end up doing, as long as ReAIM can also handle AIM file transfers too. Then I'll have this for AIM and DeleGate for Http/Ftp. My game playing friends would be out of luck, as would kazaa users, but that's probably good for them anyway. Frustratingly complicated though.
John